Abstract
AbstractThe imidazolinium chloride 8 reacts with diazomethyl compounds 3 (in the presence of an amine) or with metal derivatives of 3 under the formation of the 2‐(diazomethyl) imidazolidines 9. Compounds of the same type are received by treatment of the electron‐rich olefine 10 with 3 at elevated temperature. An analogous substitution process at 3 with the donor‐stabilized salts 13 and 17 produces stable 2‐(diazomethyl) benzthiazolines (14) and 6‐(diazomethyl) hexahydro‐1,3,5‐triazines (18) respectively.Thermolysis and photolysis of 9 mainly yield tetrahydro‐1,4‐diazines (21) by 1,2‐N‐shift of the carbene precursors 20; moreover the hitherto unknown isomerization reaction of the diazo compounds 9 to the azines 25 has been observed. In the thermal decomposition of 14 the formation of 2‐methylenbenzthiazolines (28) is preferred whereas photolysis of the same diazo compounds affords mixtures of 28 and 1,4‐benzothiazines 30. The olefines 28 are characterized by protonation (31) and reaction with the cyclic azo compound 32 (34).
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